Whitey Bulger

James Joseph "Whitey" Bulger Jr. (3 September 1929-) was the boss of the Winter Hill Gang in Boston from 1979 to 1995, succeeding Howie Winter and preceding Kevin Weeks. Bulger was known for becoming an FBI informant in order to protect his organization from justice and to have an ally in the fight against the Patriarca crime family. He was arrested in 2011 after a long manhunt, and, on 14 November 2013, he was sentenced to two consecutive life sentences for his crimes.

Early life
James Joseph Bulger Jr. was born in Boston, Massachusetts in 1929, the son of a Canadian father and an Irish mother. His family was reduced to poverty after his father lost his arm in an industrial accident, and the family moved into a South Boston housing project in 1938. "Jimmy" and his brother William Bulger grew up in the "Southie" projects, and, while James' two brothers excelled in school, Jimmy was drawn into street life. Jimmy Bulger was nicknamed "Whitey" by the police because of his blond hair, and this nickname stuck with him.

Early career
In 1943, at the age of 14, Bulger was arrested and charged with larceny. In 1948, Bulger joined the US Air Force, but he spent time in military prison for several assaults; nevertheless, he was honorably discharged in 1952. In 1956, Bulger was sent to federal prison in Atlanta for armed robbery and truck hijacking, and he volunteered to take part in the CIA's MK-ULTRA drug experimentation program in exchange for a reduced sentence. He was transferred to Alcatraz in 1959, to Leavenworth in 1962, and to Lewisburg in 1963. In 1965, he was granted parole, and he would not spend a day behind bars for 46 more years. After his release, Bulger worked as a janitor and construction worker before becoming a bookmaker and loan shark under Donald Killeen, the leader of the Killeen Gang of Boston's Irish Mob. During the war between the Killeens and the Mullin Gang, Bulger approached Winter Hill Gang leader Howie Winter and convinced him that he could end the war by killing the leaders of the two gangs, and he killed Killeen in 1972 and Mullin Gang leader Paul McGonagle in 1974.

Winter Hill boss
In 1974, Bulger formed a partnership with Stephen Flemmi and Johnny Martorano, and, in 1975, Bulger and Flemmi were recruited as FBI informants by FBI agent John Connolly, who met with Bulger in an FBI-issued car at Wollaston Beach and promised him aid in his rivalry with the Patriarca crime family and protection from the feds; Bulger went on to convince Flemmi to become an informant. In 1979, after Howie Winter was arrested for fixing horse racing, Bulger took over as boss of the Winter Hill Gang. Bulger exploited his FBI informant relationship to cover for his crimes, and he assisted the FBI in wiretapping the rival Angiulo brothers, Patriarca made men who controlled the North End of Boston. In 1982, he murdered bookmaker Louis Litif, and he also sent Martorano to murder his rivals Roger Wheeler and John B. Callahan after they cut him out of an embezzlement scheme from World Jai Alai. An associate of Bulger's, Edward Brian Halloran, went to the FBI to report Bulger's involvement in the murders, and he was murdered by Bulger after Connolly told Bulger about Halloran's betrayal. Bulger became increasingly violent and unpredictable after the passing of his mother, deteriorating his informant relationship. Later, John McIntyre informed on Bulger's plan to smuggle arms to the IRA, and Connolly again informed Bulger, who killed McIntyre. Assistant US Attorney Fred Wyshak and FBI supervisor Charles McGuire proceeded to investigate Connolly's management of Bulger's informant role, and they discovered that most of Whitey's tips were already obtained from other sources. FBI agent John Morris decided to reveal Connolly and Whitey's relationship to the Boston Globe, and a front-page story exposed the FBI's links to organized crime. During the 1990s, Connolly, Flemmi, Kevin Weeks, and Martorano were arrested, and Bulger went on the run.

On 22 June 2011, Bulger was arrested outside an apartment in Santa Monica, California, and he was extradited to Massachusetts. On 14 November 2013, he was sentenced to two consecutive life sentences plus five years for 32 counts of racketeering, money laundering, extortion, weapons charges, and complicity in 19 murders.